Head of Forward Deployed Engineering

Assort Health

• $150K — $180K *
Healthcare
5 - 7 years of experience
Job Overview by Ladders

Qualifications

  • 5+ years of software engineering experience
  • 2+ years leading customer-facing technical teams
  • Proven history of scaling implementation teams in B2B or enterprise software
  • Strong technical fundamentals with hands-on abilities
  • Experience in creating repeatable processes and tooling for scaling
  • Exceptional communication skills for interacting with diverse stakeholders
  • Willingness to travel for customer site engagements

Responsibilities

  • Scale the Forward Deployed Engineering team through hiring and developing talent
  • Own end-to-end technical delivery for major customers
  • Translate customer needs into scalable technical solutions
  • Establish deployment patterns and best practices for efficiency
  • Drive a feedback loop from field implementation to product features
  • Conduct technical discovery and troubleshoot production issues
  • Set technical standards and expectations for the team

Benefits

  • Competitive compensation including salary and stock options
  • Annual budget for professional development
  • Office setup stipend for a productive workspace
  • Comprehensive health coverage including medical, dental, and vision
  • Flexible paid time off policy
  • Provided meals and snacks for employees
  • Fitness stipend to support health and wellness
  • Commuter benefits to assist with transportation costs
  • 401(k) plan to support retirement savings
Full Job Description
About the Role

As the Head of Forward Deployed Engineering at Assort Health, you'll build and lead the team responsible for turning our AI agent platform into production systems for our largest and most complex healthcare customers. Your team sits at the intersection of engineering, product, and customer success - owning the technical implementation of health system deployments, custom EHR integrations, and workflow builds that bring AI agents to life.

You'll scale the FDE organization from a small team to 10+ engineers, establish repeatable deployment patterns, and create the feedback loop that turns field learnings into platform improvements.

What You'll Do
  • Scale the Forward Deployed Engineering team, including hiring, coaching, and developing a high-performing organization.
  • Own end-to-end technical delivery for our most strategic customers.
  • Partner closely with cross-functional teams to translate customer needs into scalable technical solutions and influence product roadmap based on field insights.
  • Establish deployment patterns, best practices, and internal tooling that enable the FDE team to move faster and scale more efficiently.
  • Drive the field-to-product feedback loop - identify patterns across implementations that should become platform features and work with product engineering to build them.
  • Be hands-on when it matters: lead technical discovery with strategic accounts, debug production issues, and set the technical bar for the team.
What We're Looking For
  • 5+ years of software engineering experience, with 2+ years leading customer-facing technical teams
  • Track record of scaling technical implementation or deployment teams in fast-growing B2B or enterprise software companies
  • Strong technical fundamentals with hands-on ability to design, build, and debug production systems alongside your team
  • Exceptional at balancing customer needs, technical feasibility, and engineering velocity - you know when to build custom vs. push for platform solutions
  • Experience building repeatable processes and tooling to scale implementation work
  • Outstanding communicator who can interface with C-suite healthcare executives, technical teams, and internal stakeholders
  • Willingness to travel to customer sites and be embedded with healthcare organizations during critical implementations


Benefits & Perks for Assorties
  • Competitive Compensation - Including salary and employee stock options so you share in our success.
  • Lifelong Learning - Annual budget for professional development, plus training opportunities to help you grow.
  • Office Setup Stipend - We'll outfit your in-office workspace so comfy as it's productive.
  • Top-Tier Health Coverage - Medical, dental, and vision insurance, because your health comes first.
  • Flexible PTO - We trust you to take the time you need to recharge and come back ready to crush it.
  • 🥗 Meals & Snacks - Lunch, dinner, and snack breaks that fuel great ideas.
  • Fitness Stipend - Your wellness matters. We reimburse monthly membership costs to support your health.
  • 🚆 Commuter Benefits - We cover eligible transportation costs to make your trip to work easier.
  • 401(k) - Build your retirement savings.

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